1,1,3,3-Tetramethylguanidine → HCID 178467224, Verbindung

HRID 1758759Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1758759
Br[C:2](=[CH:6]OCC)[C:3](=[O:5])[CH3:4].Cl.[OH:11][CH2:12][C:13]([NH2:15])=[NH:14].CN(C)C(N(C)C)=N>CC(C)=O>[OH:11][CH2:12][C:13]1[NH:14][CH:6]=[C:2]([C:3](=[O:5])[CH3:4])[N:15]=1

Komponenten

5

Edukt 3

HCID 664601,1,3,3-TetramethylguanidineHCID 122173662-Hydroxy-acetamidine hydrochlorideHCID 534237433-Bromo-4-ethoxybut-3-EN-2-one

Produkt 1

HCID 178467224HCID 178467224, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

9.7 g (0.05 mol) of 3-bromo-4-ethoxy-3-buten-2-one was combined with 5.53 (0.05 mol) of hydroxyacetamidine hydrochloride in 100 ml acetone to form a slurry. To the slurry at 25° was added 11.5 g (0.1 mol) of 1,1,3,3-tetramethylguanidine over a period of 5 minutes. After stirring for 48 hours the slurry was filtered and the mother liquors were concentrated in vacuo to an oil which was chromatographed on silica gel 60 (E. Merck) using chloroform as eluent to give 1.48 g (21%) of 2-hydroxymethyl-4-acetylimidazole, mp 147°-148°. nmr (DMSO-d6) (δ): 7.73 (s, 1H); 5.46 (very broad s, 1H); 4.5 (broad s, 2H); 2.4 (s, 3H).

Aufarbeitung

  1. customto form a slurry
  2. filtrationwas filtered
  3. concentrationthe mother liquors were concentrated in vacuo to an oil which
  4. customwas chromatographed on silica gel 60 (E. Merck)

Quellen und Nachweise

ORD-Eintrag
ord-e850f63d307542a3a6e13ce379bb570b
Quelldatensatz
uspto-grants-1983_02
Patentnummer
US04374843

Notizen zur Reaktion

Wird geladen…